Literature DB >> 12553820

Catalytic asymmetric silane alcoholysis: practical access to chiral silanes.

Darby R Schmidt1, Steven J O'Malley, James L Leighton.   

Abstract

A new asymmetric synthesis of chiral silanes has been developed. Chiral phosphine-modified copper complexes catalyze the alcoholysis of prochiral dihydrosilanes with good to excellent stereoselectivity at silicon. The application of this methodology to the tandem silylformylation-allylsilylation of alkynes has been demonstrated.

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Year:  2003        PMID： 12553820     DOI： 10.1021/ja0283201

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  11 in total

1.  Total synthesis of dolabelide D.

Authors:  Peter K Park; Steven J O'Malley; Darby R Schmidt; James L Leighton
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

2.  Development of a Double Allylboration Reagent Targeting 1,5-syn-(E)-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin.

Authors:  Philippe Nuhant; Jeremy Kister; Ricardo Lira; Achim Sorg; William R Roush
Journal:  Tetrahedron       Date:  2011-09-02       Impact factor: 2.457

3.  Brønsted acid catalyzed asymmetric propargylation of aldehydes.

Authors:  Pankaj Jain; Hao Wang; Kendall N Houk; Jon C Antilla
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-28       Impact factor: 15.336

4.  Toward more "ideal" polyketide natural product synthesis: a step-economical synthesis of zincophorin methyl ester.

Authors:  Tyler J Harrison; Stephen Ho; James L Leighton
Journal:  J Am Chem Soc       Date:  2011-04-27       Impact factor: 15.419

5.  Ketone hydrosilylation with sugar silanes followed by intramolecular aglycone delivery: an orthogonal glycosylation strategy.

Authors:  Zachary A Buchan; Scott J Bader; John Montgomery
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Enantioselective Si-H Insertion Reactions of Diarylcarbenes for the Synthesis of Silicon-Stereogenic Silanes.

Authors:  Jake R Jagannathan; James C Fettinger; Jared T Shaw; Annaliese K Franz
Journal:  J Am Chem Soc       Date:  2020-06-24       Impact factor: 15.419

7.  An "aprotic" Tamao oxidation/syn-selective tautomerization reaction for the efficient synthesis of the C1-C9 fragment of fludelone.

Authors:  Tyler J Harrison; Philippe M A Rabbat; James L Leighton
Journal:  Org Lett       Date:  2012-09-05       Impact factor: 6.005

8.  Tandem silylformylation-crotylsilylation/Tamao oxidation of internal alkynes: a remarkable example of generating complexity from simplicity.

Authors:  Jared T Spletstoser; Michael J Zacuto; James L Leighton
Journal:  Org Lett       Date:  2008-12-18       Impact factor: 6.005

9.  Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic silicon-bridged arylpyridinones.

Authors:  Ryo Shintani; Ryo Takano; Kyoko Nozaki
Journal:  Chem Sci       Date:  2015-11-09       Impact factor: 9.825

10.  Conformational rigidity of silicon-stereogenic silanes in asymmetric catalysis: A comparative study.

Authors:  Sebastian Rendler; Martin Oestreich
Journal:  Beilstein J Org Chem       Date:  2007-02-08       Impact factor: 2.883
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